Carbamoylcarboxamides

ABSTRACT

Carbamoylcarboxamides of the general formula I ##STR1## and their salts (R 1  is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or an unsubstituted or substituted nonaromatic carbo- or heterocycle; 
     R 2  is H or unhalogenated or halogenated alkyl or cycloalkyl; 
     R 3  is unsubstituted or substituted alkyl, cycloalkyl or phenylalkyl; 
     R 4  is H or one of the radicals R 3  or 
     R 3  and R 4 , together with the C atom to which they are bonded, are an unsubstituted or substituted carbo- or heterocycle; 
     R 5  independently of these is one of the radicals R 2  ; 
     X independently of one another is hydrogen, unsubstituted or substituted alkyl and/or alkenyl; 
     Y independently of one another and of these is one of the radicals X; 
     p,q independently of one another are 0, 1 or 2; 
     R 6  is halogen, cyano, nitro or unsubstituted or substituted alkyl, alkoxy, alkylthio or an unsubstituted or substituted phenyl group bonded via oxygen or sulfur; 
     r is 0, 1, 2 or 3), 
     and compositions containing them, processes for preparation, and the use of the compounds I and the compositions are described.

The present invention relates to carbamoylcarboxamides of the generalformula I ##STR2## and their salts, where the variables have thefollowing meanings: R¹ is C₁ -C₈ -alkyl, C₂ -C₈ -alkenyl or C₂ -C₈-alkynyl, it being possible for these radicals to be partially orcompletely halogenated and/or to carry one to three of the followinggroups: cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁-C₄ -alkoxycarbonyl, C₃ -C₇ -cycloalkyl, C₃ -C₇ -cycloalkenyl, aryl,aryloxy and heteroaryl, it being possible for the cyclic and aromaticrings of these groups to carry one to three of the followingsubstituents: halogen, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxyalkyl, C₁ -C₄-haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁-C₄ -alkoxycarbonyl, aryl, aryloxy and heteroaryl,

C₃ -C₇ -cycloalkyl or C₃ -C₇ -cycloalkenyl, it being possible for theseradicals to be partially or completely halogenated and/or to carry oneto three of the following groups: cyano, C₁ -C₄ -alkyl, C₁ -C₄-alkoxyalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁-C₄ -alkylthio, C₁ -C₄ -alkoxycarbonyl, aryl, aryloxy and aryl-(C₁-C₄)-alkyl, it being possible for the aromatic rings of these groups inturn to carry one to three of the following substituents: halogen,cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxyalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkoxycarbonyl,aryl and aryloxy,

a nonaromatic 4- to 8-membered ring which, as ring members, in additionto carbon can further contain one or two of the heteroatoms oxygen,sulfur and nitrogen, it being possible for the carbon atoms in the ringto carry one or two of the following groups: halogen, cyano, C₁ -C₄-alkyl, C₁ -C₄ -alkoxyalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkoxycarbonyl, aryl andaryloxy, and the second and any further nitrogen atom as a heteroatom inthe ring carrying hydrogen or a C₁ -C₄ -alkyl group;

R² is hydrogen, or C₁ -C₈ -alkyl or C₃ -C₇ -cycloalkyl which can bepartially or completely halogenated;

R³ is C₁ -C₈ -alkyl, it being possible for this radical to carry one tothree of the following groups: halogen, cyano, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio and C₁ -C₄ -alkoxycarbonyl,

C₃ -C₇ -cycloalkyl or phenyl-(C₁ -C₄)-alkyl, it being possible for therings of these radicals to carry one to three of the following groups:halogen, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxyalkyl, C₁ -C₄ -haloalkyl,C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkoxycarbonyl, aryl and aryloxy;

R⁴ is hydrogen or one of the radicals R³ or

R³ and R⁴, together with the C atom to which they are bonded, are a 4-to 8-membered ring which, as ring members, in addition to carbon canfurther contain one or two of the heteroatoms oxygen, sulfur andnitrogen, it being possible for the carbon atoms in the ring to carryone or two of the following groups: halogen, cyano, C₁ -C₄ -alkyl, C₁-C₄ -alkoxyalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy,C₁ -C₄ -alkylthio, C₁ -C₄ -alkoxycarbonyl, aryl and aryloxy, andnitrogen as a heteroatom carrying hydrogen or a C₁ -C₄ -alkyl group;

R⁵ independently of these is one of the radicals R² ;

X independently of one another is hydrogen, C₁ -C₈ -alkyl and/or C₂ -C₈-alkenyl, it being possible for these radicals to be partially orcompletely halogenated and/or to carry one to three of the followinggroups: cyano, C₁ -C₄ -alkoxyalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy,C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio and C₁ -C₄ -alkoxycarbonyl, aryland aryloxy;

Y independently of one another and of these is one of the radicals X;

p,q independently of one another are 0, 1 or 2;

R⁶ is halogen, cyano, nitro, C₁ -C₈ -alkyl, C₁ -C₄ -alkoxyalkyl, C₁ -C₄-haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁-C₄ -haloalkylthio or a phenyl group bonded via oxygen or sulfur, whichis unsubstituted or can carry one to three of the followingsubstituents: halogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy, where R⁶ for r>1can be various radicals from those mentioned;

r is 0, 1, 2 or 3.

The invention additionally relates to processes for preparing thecompounds I. The invention furthermore relates to compositions whichcontain the compounds I or their salts, a method of preparingcompositions of this type and a method for controlling harmful fungi andthe use of the compounds I, their salts or the compositions therefor.

Compounds of type I having fungicidal action have already been disclosedin the following publications: in particular EP-A 554 729 and DE-A 43 21897, in addition EP-A 398 072, EP-A 425 925, EP-A 472 996, EP-A 477 639,EP-A 485 794, EP-A 493 683, EP-A 496 239, EP-A 550 788 and EP-A 587110). However, the known compounds are still not satisfactory withrespect to their fungicidal action.

It is an object of the present invention to provide novelcarbamoylcarboxamides having an improved action against harmful fungi.

We have now found that this object is achieved by the compounds Idefined at the outset, their salts and compositions containing them.

We have furthermore found processes for preparing the compounds I andthe compositions containing them and additionally a method ofcontrolling harmful fungi and the use of the compounds I, their salts orthe compositions therefor.

The subject matter of German Patent Application P 44 31 467.1 which isrelevant to the present invention is hereby included.

The compounds I can be prepared in a manner known per se starting fromthe corresponding carbamoylcarboxylic acids II. The compounds I arepreferably obtained by the processes A and B described in the following(the Houben-Weyl literature citations relate to: Houben-Weyl, Methodender Organischen Chemie (Methods of Organic Chemistry), 4th edition,Thieme Verlag, Stuttgart).

Process A

The carbamoylcarboxamides I are obtained by reacting carbamoylcarboxylicacids II with the amines III. ##STR3##

The carbamoylcarboxylic acids II are known or can be prepared by knownmethods, especially starting from the amino acids on which they arebased (cf. Houben-Weyl, Volume 15/1, page 46 to page 305, especiallypage 117 to page 125).

The amines III are likewise known or can be easily obtained (cf.Organikum, VEB Deutscher Verlag der Wissenschaften, 15th edition,Berlin, 1977, page 610 ff.; Houben-Weyl, Volume 15/1, page 648-665;Indian J. Chem. 10 (1972), page 366).

This process A is preferably carried out in such a way that thecarbamoylcarboxylic acids II are first converted to carboxyl-activatedderivatives, especially to acyl cyanides or anhydrides (cf. TetrahedronLetters, Volume 18 (1973), page 1595 to page 1598, or Houben-Weyl,Volume 15/1, page 28 to page 32). These derivatives are then reactedwith the amines III in the presence of bases.

A suitable reaction for preparing the-carboxyl-activated acyl cyanidesis eg. the reaction of the carbamoylcarboxylic acids II with diethylcyanophosphonate, especially in an inert solvent such as tetrahydrofuranor toluene.

To prepare the carboxyl-activated anhydrides, the reaction of thecarbamoylcarboxylic acid II with carbonyl chlorides such as isobutylchloroformate in the presence of bases and if appropriate in an inertsolvent such as toluene or tetrahydrofuran is preferred.

The reaction of the amines III with the carboxyl-activatedcarbamoylcarboxylic acids II is preferably carried out in a solvent suchas dichloromethane, tetrahydrofuran or toluene.

The bases used can in particular be the amines III themselves, thelatter customarily being recovered from the crude product.

In a preferred embodiment of this process step, the carbamoylcarboxylicacid II, the amine III, the reagent suitable for the production of thecarboxyl-activated derivative of the carbamoylcarboxylic acid II and thebase are reacted in a one-pot process, if appropriate in an inertsolvent, and the crude product is then worked up to thecarbamoylcarboxamide I in a manner known per se.

Process B

The carbamoylcarboxamides I are obtained by converting thecarbamoylcarboxamides I in which the group R¹ --O--(CO) is a protectivegroup which can be removed in a manner known per se to amino acid amidesIV and reacting these with chloroformic acid ester V in the presence ofa base.

Step Ba: Preparation of the amino acid amides IV ##STR4##

The removal of the group R¹ --O--(CO) from the carbamoylcarboxamides Ican be carried out in a manner known per se (cf. Houben-Weyl, Volume15/1, page 46 to page 305, especially page 126 to page 129).

Suitable removable groups contain, as the R¹ radical, a tert-butyl groupor the benzyl group.

If R¹ =tert-butyl, for example, removal is customarily carried out byreaction with an acid, in particular a protic acid such as eg.hydrochloric acid or trifluoroacetic acid (ibid., page 126 to page 129).

The carbamoylcarboxamides I suitable as starting substances can beobtained by known processes (cf. Houben-Weyl, Volume 15/1, page 28 topage 32) or in particular by process A according to the invention.

Step Bb: Preparation of the carbamoylcarboxamides I ##STR5##

The amino acid amides IV resulting from the synthesis step (Ba) arereacted with the chloroformic acid esters V in the presence of bases.

The chloroformic acid esters V are generally known or can be prepared byknown processes.

The reaction is preferably carried out in an organic solvent, especiallytoluene, methylene chloride or tetrahydrofuran, or mixtures of these.

Suitable bases are equally inorganic and organic bases, organic basesand among them, in turn, tertiary amines such as triethylamine, pyridineand N-methylpiperidine being preferred.

As a rule, the reaction is carried out at from -40° to 50° C.,preferably from -10° to 20° C.

Otherwise, the carrying-out of this reaction is familiar to the personskilled in the art, so no further details are needed therefor (cf.Houben-Weyl, Volume 15/1, page 117 to page 139).

The reaction mixtures obtained by processes A and B are worked up in acustomary manner, eg. by mixing with water, separating the phases andwhere appropriate chromatographically purifying the crude products. Theintermediate and final products are in some cases obtained in the formof colorless or slightly brownish, viscous oils, which can be freed fromvolatile constituents under reduced pressure and at moderately elevatedtemperature. If the intermediates and final products are obtained assolids, the purification can also be carried out, for example, byrecrystallizing or digesting.

Depending on the nature of the substituents, where appropriate thecompounds of the formula I can be obtained as geometric and/or opticalisomers or isomer mixtures. Both the pure isomers and the mixtures ofthe isomers have fungicidal action.

Also part of the invention are the salts, especially of the acid-stablecompounds I which contain basic centers, especially basic nitrogenatoms, in particular with mineral acids such as sulfuric acid andphosphoric acid or Lewis acids such as zinc chloride. Customarily, inthis case the nature of the salt does not matter. In the context of theinvention those salts are preferred which do not harm the plants,surfaces, materials or spaces to be kept free from harmful fungi and donot adversely affect the action of the compounds I. Agriculturallyutilizable salts of this type are particularly important.

The salts of the compounds I are accessible in a manner known per se,especially by reacting the corresponding carbamoylcarboxamides I withsaid acids in water or an inert organic solvent at from -80° to 120° C.,preferably 0° to 60° C.

As a rule, the preparation of the salts is independent of the pressure,which is why the reaction is especially carried out at atmosphericpressure.

In the definition of the compounds I given at the outset, collectiveterms were used which are representative of the following substituents:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: straight-chain or branched alkyl groups having 1 to 8 carbonatoms, eg. C₁ -C₆ -alkyl such as methyl, ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 1,2-dimethylpropyl, 1-ethylpropyl, n-hexyl,r-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl,1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

haloalkyl or partially or completely halogenated alkyl: straight-chainor branched alkyl groups having 1 to 4 or 8 carbon atoms (as mentionedabove), it being possible in these groups for the hydrogen atoms to bepartially or completely replaced by halogen atoms (as mentioned above),eg. C₁ -C₂ -haloalkyl such as chloromethyl, dichloromethyl,trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

alkoxy: straight-chain or branched alkoxy groups having 1 to 4 carbonatoms, eg. C₁ -C₃ -alkoxy such as methoxy, ethoxy, propoxy and1-methylethoxy;

alkoxyalkyl: straight-chain or branched alkyl groups having 1 to 8carbon atoms (as mentioned above) which, in any desired position, carrya straight-chain or branched alkoxy group (as mentioned above), having,in the case of C₁ -C₄ -alkoxyalkyl, 1 to 4 carbon atoms, such asmethoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl,1-methoxyethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl,2-n-propoxyethyl and 2-butoxyethyl;

haloalkoxy: straight-chain or branched alkoxy groups having 1 to 4carbon atoms (as mentioned above), it being possible in these groups forthe hydrogen atoms to be partially or completely replaced by halogenatoms (as mentioned above), eg. C₁ -C₂ -haloalkoxy such aschloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy,difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy,dichlorofluoromethoxy, chlorodifluoromethoxy, 1-fluoroethoxy,2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy andpentafluoroethoxy;

alkylthio: straight-chain or branched alkyl groups having 1 to 4 carbonatoms (as mentioned above) which are bonded to the structure via asulfur atom (--S--), eg. C₁ -C₄ -alkylthio such as methylthio,ethylthio, propylthio, 1-methylethylthio, n-butylthio andtert-butylthio; alkoxycarbonyl: straight-chain or branched alkoxy groupshaving 1 to 4 C atoms (as mentioned above), which are bonded to thestructure via a carbonyl group (--CO--);

alkenyl: straight-chain or branched alkenyl groups having 2 to 8 carbonatoms and a double bond in any desired position, eg. C₂ -C₆ -alkenylsuch as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl,2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

alkynyl: straight-chain or branched alkynyl groups having 2 to 8 carbonatoms and a triple bond in any desired position, eg. C₂ -C₆ -alkynylsuch as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl,3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl,4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl,3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl,3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl,1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

cycloalkyl: monocyclic alkyl groups having 3 to 7 carbon ring members,eg. C₃ -C₇ -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl and cycloheptyl;

cycloalkenyl: monocyclic alkyl groups having 5 to 7 carbon ring memberswhich contain one or more double bonds, eg. C₅ -C₇ -cycloalkenyl such ascyclopentenyl, cyclohexenyl and cycloheptenyl;

nonaromatic 4- to 8-membered rings which, as ring members, in additionto carbon further contain one or two oxygen, sulfur or nitrogen atoms,such as saturated 5- or 6-membered rings having 1 or 2 nitrogen and/oroxygen atoms such as 3-tetrahydrofuranyl, 1-piperidinyl, 2-piperidinyl,3-piperidinyl, 4-piperidinyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl,4-tetrahydropyranyl, 2-morpholinyl and 3-morpholinyl;

aryl: monocyclic or polycyclic aromatic groups having 6 to 10 C atomssuch as phenyl and naphthyl;

arylalkyl: aryl groups (as mentioned above) which in the case ofaryl-(C₁ -C₄)-alkyl are bonded to the structure via alkyl groups having1 to 4 carbon atoms (as mentioned above), eg. phenyl-(C₁ -C₄)-alkyl suchas benzyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 1-phenylethyl,1-phenylpropyl and 1-phenylbutyl;

aryloxy: aryl groups (as mentioned above) which are bonded to thestructure via an oxygen atom (--O--), such as phenoxy, 1-naphthoxy and2-naphthoxy;

heteroaryl: aromatic mono- or polycyclic radicals which in addition tocarbon ring members can additionally contain 1 to 4 nitrogen atoms or 1to 3 nitrogen atoms and an oxygen or a sulfur atom or an oxygen or asulfur atom, eg.:

5-membered heteroaryl, containing 1 to 3 nitrogen atoms: 5-membered ringheteroaryl groups which in addition to carbon atoms can contain 1 to 3nitrogen atoms as ring members, eg. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl,4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yland 1,3,4-triazol-2-yl;

5-membered heteroaryl, containing 1 to 4 nitrogen atoms or 1 to 3nitrogen atoms and 1 sulfur or oxygen atom or 1 oxygen or sulfur atom:5-membered ring heteroaryl groups which in addition to carbon atoms cancontain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur oroxygen atom or 1 oxygen or sulfur atom as ring members, eg. 2-furyl,3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl,4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl,5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl,4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl,2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl,1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl,1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl;

benzo-fused 5-membered heteroaryl, containing 1 to 3 nitrogen atoms or 1nitrogen atom and/or an oxygen or sulfur atom: 5-membered ringheteroaryl groups which in addition to carbon atoms can contain 1 to 4nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom or 1oxygen or sulfur atom as ring members, and in which 2 adjacent carbonring members or 1 nitrogen and 1 adjacent carbon ring member can bebridged by a buta-1,3-diene-1,4-diyl group;

5-membered heteroaryl bonded via nitrogen and containing 1 to 4 nitrogenatoms, or benzo-fused 5-membered heteroaryl bonded via nitrogen andcontaining 1 to 3 nitrogen atoms: 5-membered ring heteroaryl groupswhich in addition to carbon atoms can contain 1 to 4 nitrogen atoms or 1to 3 nitrogen atoms as ring members, and in which 2 adjacent carbon ringmembers or a nitrogen and an adjacent carbon ring member can be bridgedby a buta-1,3-diene-1,4-diyl group, these rings being bonded to thestructure via one of the nitrogen ring members;

6-membered heteroaryl, containing 1 to 3 or 1 to 4 nitrogen atoms:6-membered ring heteroaryl groups which in addition to carbon atoms cancontain 1 to 3 or 1 to 4 nitrogen atoms as ring members, eg.2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;

benzo-fused 6-membered heteroaryl, containing 1 to 4 nitrogen atoms:6-membered ring heteroaryl groups in which 2 adjacent carbon ringmembers can be bridged by a buta-1,3-diene-1,4-diyl group, eg.quinoline, isoquinoline, quinazoline and quinoxaline.

The statement partially or completely halogenated is intended to expressthat in the groups characterized in this way the hydrogen atoms can bepartially or completely replaced by identical or different halogenatoms, as mentioned above.

With respect to their action against harmful fungi, compounds I arepreferred in which the radicals have the following meanings, to bespecific on their own per se or in combination. The groups mentioned inthe meanings of radicals in the following can also be substitutedaccording to the claims.

R¹ is C₁ -C₈ -alkyl and especially C₁ -C₄ -alkyl;

R² is hydrogen or C₁ -C₈ -alkyl;

R³ is C₁ -C₈ -alkyl, C₃ -C₇ -cycloalkyl or phenyl-(C₁ -C₄)-alkyl,especially C₁ -C₈ -alkyl and in particular C₃ -alkyl, preferablyisopropyl;

R⁴ is C₁ -C₈ -alkyl and especially hydrogen;

R⁵ is hydrogen;

X independently of one another is hydrogen or C₁ -C₈ -alkyl, preferablyC₁ -C₈ -alkyl, especially C₁ -C₄ -alkyl;

Y independently of one another is hydrogen or C₁ -C₈ -alkyl, especiallyhydrogen;

p is 0 or 1, especially 1;

q is 0 or 1, especially 0;

R⁶ is halogen or C₁ -C₈ -alkyl, especially halogen sic! or C₁ -C₄-alkyl;

r is 0 or 1, especially 0.

With respect to their use, the compounds I compiled in the followingTables 1 to 5 are very particularly preferred.

                  TABLE 1                                                         ______________________________________                                         ##STR6##                                                                     No.     R.sup.1       X          R.sup.6                                      ______________________________________                                        1.2     C(CH.sub.3).sub.3                                                                           CH.sub.2 CH.sub.3                                                                        H                                            1.3     C(CH.sub.3).sub.3                                                                           CH.sub.3   1-Cl                                         1.4     C(CH.sub.3).sub.3                                                                           CH.sub.3   3-Cl                                         1.5     C(CH.sub.3).sub.3                                                                           CH.sub.3   4-Cl                                         1.6     C(CH.sub.3).sub.3                                                                           CH.sub.3   5-Cl                                         1.7     C(CH.sub.3).sub.3                                                                           CH.sub.3   6-Cl                                         1.8     C(CH.sub.3).sub.3                                                                           CH.sub.3   7-Cl                                         1.9     C(CH.sub.3).sub.3                                                                           CH.sub.3   8-Cl                                         1.10    C(CH.sub.3).sub.3                                                                           CH.sub.3   1-OCH.sub.3                                  1.11    C(CH.sub.3).sub.3                                                                           CH.sub.3   3-OCH.sub.3                                  1.12    C(CH.sub.3).sub.3                                                                           CH.sub.3   4-OCH.sub.3                                  1.13    C(CH.sub.3).sub.3                                                                           CH.sub.3   5-OCH.sub.3                                  1.14    C(CH.sub.3).sub.3                                                                           CH.sub.3   6-OCH.sub.3                                  1.15    C(CH.sub.3).sub.3                                                                           CH.sub.3   7-OCH.sub.3                                  1.16    C(CH.sub.3).sub.3                                                                           CH.sub.3   5,6-(OCH.sub.3).sub.2                        1.17    C(CH.sub.3).sub.3                                                                           CH.sub.3   5,7-(OCH.sub.3).sub.2                        1.18    C(CH.sub.3).sub.3                                                                           CH.sub.3   1-CH.sub.3                                   1.19    C(CH.sub.3).sub.3                                                                           CH.sub.3   3-CH.sub.3                                   1.20    C(CH.sub.3).sub.3                                                                           CH.sub.3   4-CH.sub.3                                   1.21    C(CH.sub.3).sub.3                                                                           CH.sub.3   5-CH.sub.3                                   1.23    C(CH.sub.3).sub.3                                                                           CH.sub.3   7-CH.sub.3                                   1.24    C(CH.sub.3).sub.3                                                                           CH.sub.3   5,6-(CH.sub.3).sub.2                         1.25    C(CH.sub.3).sub.3                                                                           CH.sub.3   5,7-(CH.sub.3).sub.2                         1.26    C(CH.sub.3).sub.3                                                                           CH.sub.3   1-OH                                         1.28    CH(CH.sub.3).sub.2                                                                          CH.sub.2 CH.sub.3                                                                        H                                            1.29    CH(CH.sub.3).sub.2                                                                          CH.sub.3   1-Cl                                         1.30    CH(CH.sub.3).sub.2                                                                          CH.sub.3   3-Cl                                         1.31    CH(CH.sub.3).sub.2                                                                          CH.sub.3   4-Cl                                         1.32    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5-Cl                                         1.33    CH(CH.sub.3).sub.2                                                                          CH.sub.3   6-Cl                                         1.34    CH(CH.sub.3).sub.2                                                                          CH.sub.3   7-Cl                                         1.35    CH(CH.sub.3).sub.2                                                                          CH.sub.3   8-Cl                                         1.36    CH(CH.sub.3).sub.2                                                                          CH.sub.3   1-OCH.sub.3                                  1.37    CH(CH.sub.3).sub.2                                                                          CH.sub.3   3-OCH.sub.3                                  1.38    CH(CH.sub.3).sub.2                                                                          CH.sub.3   4-OCH.sub.3                                  1.39    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5-OCH.sub.3                                  1.41    CH(CH.sub.3).sub.2                                                                          CH.sub.3   7-OCH.sub.3                                  1.42    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5,6-(OCH.sub.3).sub.2                        1.43    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5,7-(OCH.sub.3).sub.2                        1.44    CH(CH.sub.3).sub.2                                                                          CH.sub.3   1-CH.sub.3                                   1.45    CH(CH.sub.3).sub.2                                                                          CH.sub.3   3-CH.sub.3                                   1.46    CH(CH.sub.3).sub.2                                                                          CH.sub.3   4-CH.sub.3                                   1.47    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5-CH.sub.3                                   1.49    CH(CH.sub.3).sub.2                                                                          CH.sub.3   7-CH.sub.3                                   1.50    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5,6-(CH.sub.3).sub.2                         1.51    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5,7-(CH.sub.3).sub.2                         1.52    CH(CH.sub.3).sub.2                                                                          CH.sub.3   1-OH                                         1.54    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.2 CH.sub.3                                                                        H                                            1.55    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   1-Cl                                         1.56    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   3-Cl                                         1.57    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   4-Cl                                         1.58    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5-Cl                                         1.59    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   6-Cl                                         1.60    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   7-Cl                                         1.61    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   8-Cl                                         1.62    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   1-OCH.sub.3                                  1.63    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   3-OCH.sub.3                                  1.64    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   4-OCH.sub.3                                  1.65    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5-OCH.sub.3                                  1.66    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   6-OCH.sub.3                                  1.67    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   7-OCH.sub.3                                  1.68    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5,6-(OCH.sub.3).sub.2                        1.69    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5,7-(OCH.sub.3).sub.2                        1.70    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   1-CH.sub.3                                   1.71    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   3-CH.sub.3                                   1.72    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   4-CH.sub.3                                   1.73    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5-CH.sub.3                                   1.75    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   7-CH.sub.3                                   1.76    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5,6-(CH.sub.3).sub.2                         1.77    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5,7-(CH.sub.3).sub.2                         1.78    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   1-OH                                         1.79    C(CH.sub.3).sub.3                                                                           CH.sub.3   6-CN                                         1.80    CH(CH.sub.3).sub.2                                                                          CH.sub.3   6-CN                                         1.81    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   6-CN                                         1.82    C(CH.sub.3).sub.3                                                                           CH.sub.3   5-CN                                         1.83    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5-CN                                         1.84    CH(CH.sub.3)C.sub.2 H.sub.5                                                                 CH.sub.3   5-CN                                         ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                         ##STR7##                                                                     No.     R.sup.1       X          R.sup.6                                      ______________________________________                                        2.2     C(CH.sub.3).sub.3                                                                           CH.sub.2 CH.sub.3                                                                        H                                            2.3     C(CH.sub.3).sub.3                                                                           CH.sub.3   2-Cl                                         2.4     C(CH.sub.3).sub.3                                                                           CH.sub.3   3-Cl                                         2.6     C(CH.sub.3).sub.3                                                                           CH.sub.3   5-Cl                                         2.7     C(CH.sub.3).sub.3                                                                           CH.sub.3   6-Cl                                         2.8     C(CH.sub.3).sub.3                                                                           CH.sub.3   7-Cl                                         2.9     C(CH.sub.3).sub.3                                                                           CH.sub.3   8-Cl                                         2.10    C(CH.sub.3).sub.3                                                                           CH.sub.3   2-OCH.sub.3                                  2.11    C(CH.sub.3).sub.3                                                                           CH.sub.3   3-OCH.sub.3                                  2.12    C(CH.sub.3).sub.3                                                                           CH.sub.3   4-OCH.sub.3                                  2.13    C(CH.sub.3).sub.3                                                                           CH.sub.3   5-OCH.sub.3                                  2.14    C(CH.sub.3).sub.3                                                                           CH.sub.3   6-OCH.sub.3                                  2.15    C(CH.sub.3).sub.3                                                                           CH.sub.3   7-OCH.sub.3                                  2.16    C(CH.sub.3).sub.3                                                                           CH.sub.3   5,6-(OCH.sub.3).sub.2                        2.17    C(CH.sub.3).sub.3                                                                           CH.sub.3   5,7-(OCH.sub.3).sub.2                        2.18    C(CH.sub.3).sub.3                                                                           CH.sub.3   2-CH.sub.3                                   2.19    C(CH.sub.3).sub.3                                                                           CH.sub.3   3-CH.sub.3                                   2.20    C(CH.sub.3).sub.3                                                                           CH.sub.3   4-CH.sub.3                                   2.21    C(CH.sub.3).sub.3                                                                           CH.sub.3   5-CH.sub.3                                   2.22    C(CH.sub.3).sub.3                                                                           CH.sub.3   6-CH.sub.3                                   2.23    C(CH.sub.3).sub.3                                                                           CH.sub.3   7-CH.sub.3                                   2.24    C(CH.sub.3).sub.3                                                                           CH.sub.3   5,6-(CH.sub.3).sub.2                         2.25    C(CH.sub.3).sub.3                                                                           CH.sub.3   5,7-(CH.sub.3).sub.2                         2.26    C(CH.sub.3).sub.3                                                                           CH.sub.3   2-OH                                         2.28    CH(CH.sub.3).sub.2                                                                          CH.sub.2 CH.sub.3                                                                        H                                            2.29    CH(CH.sub.3).sub.2                                                                          CH.sub.3   2-Cl                                         2.30    CH(CH.sub.3).sub.2                                                                          CH.sub.3   3-Cl                                         2.32    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5-Cl                                         2.33    CH(CH.sub.3).sub.2                                                                          CH.sub.3   6-Cl                                         2.34    CH(CH.sub.3).sub.2                                                                          CH.sub.3   7-Cl                                         2.35    CH(CH.sub.3).sub.2                                                                          CH.sub.3   8-Cl                                         2.36    CH(CH.sub.3).sub.2                                                                          CH.sub.3   2-OCH.sub.3                                  2.37    CH(CH.sub.3).sub.2                                                                          CH.sub.3   3-OCH.sub.3                                  2.38    CH(CH.sub.3).sub.2                                                                          CH.sub.3   4-OCH.sub.3                                  2.39    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5-OCH.sub.3                                  2.40    CH(CH.sub.3).sub.2                                                                          CH.sub.3   6-OCH.sub.3                                  2.41    CH(CH.sub.3).sub.2                                                                          CH.sub.3   7-OCH.sub.3                                  2.42    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5,6-(OCH.sub.3).sub.2                        2.43    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5,7-(OCH.sub.3).sub.2                        2.44    CH(CH.sub.3).sub.2                                                                          CH.sub.3   2-CH.sub.3                                   2.45    CH(CH.sub.3).sub.2                                                                          CH.sub.3   3-CH.sub.3                                   2.46    CH(CH.sub.3).sub.2                                                                          CH.sub.3   4-CH.sub.3                                   2.47    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5-CH.sub.3                                   2.48    CH(CH.sub.3).sub.2                                                                          CH.sub.3   6-CH.sub.3                                   2.49    CH(CH.sub.3).sub.2                                                                          CH.sub.3   7-CH.sub.3                                   2.50    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5,6-(CH.sub.3).sub.2                         2.51    CH(CH.sub.3).sub.2                                                                          CH.sub.3   5,7-(CH.sub.3).sub.2                         2.52    CH(CH.sub.3).sub.2                                                                          CH.sub.3   2-OH                                         2.54    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.2 CH.sub.3                                                                        H                                            2.55    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   2-Cl                                         2.56    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   3-Cl                                         2.58    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5-Cl                                         2.59    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   6-Cl                                         2.60    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   7-Cl                                         2.61    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   8-Cl                                         2.62    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   2-OCH.sub.3                                  2.63    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   3-OCH.sub.3                                  2.64    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   4-OCH.sub.3                                  2.65    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5-OCH.sub.3                                  2.66    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   6-OCH.sub.3                                  2.67    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   7-OCH.sub.3                                  2.68    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5,6-(OCH.sub.3).sub.2                        2.69    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5,7-(OCH.sub.3).sub.2                        2.70    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   2-CH.sub.3                                   2.71    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   3-CH.sub.3                                   2.72    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   4-CH.sub.3                                   2.73    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5-CH.sub.3                                   2.74    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   6-CH.sub.3                                   2.75    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   7-CH.sub.3                                   2.76    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5,6-(CH.sub.3).sub.2                         2.77    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   5,7-(CH.sub.3).sub.2                         2.78    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3   2-OH                                         ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                         ##STR8##                                                                     No.        R.sup.1       X         Y                                          ______________________________________                                        3.1        C(CH.sub.3).sub.3                                                                           H         H                                          3.3        C(CH.sub.3).sub.3                                                                           H         CH.sub.3                                   3.4        CH(CH.sub.3).sub.2                                                                          H         H                                          3.6        CH(CH.sub.3).sub.2                                                                          H         CH.sub.3                                   3.7        CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               H         H                                          3.8        CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               CH.sub.3  H                                          3.9        CH(CH.sub.3)(C.sub.2 H.sub.5)                                                               H         CH.sub.3                                   ______________________________________                                    

The novel compounds of the formula I and their salts are suitable forcontrolling harmful fungi.

The novel compounds or their salts can be applied by spraying,atomizing, dusting, scattering or watering, for example in the form ofdirectly sprayable solutions, powders, suspensions, even high-percentageaqueous, oily or other suspensions or dispersions, emulsions, oildispersions, pastes, dusting compositions, scattering compositions orgranules. The application forms depend on the intended uses; in eachcase they should if possible ensure the finest dispersion of the activecompounds according to the invention.

Normally, in the treatment of plants the plants are sprayed or dustedwith the active compounds or the seeds of the plants are treated withthe active compounds.

The formulations are prepared in a known manner, eg. by extending theactive compound with solvents and/or carriers, if desired usingemulsifiers and dispersants, where if water is used as a diluent otherorganic solvents can also be used as auxiliary solvents. Suitableauxiliaries for this purpose are mainly: solvents such as aromatics (eg.xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg.petroleum fractions), alcohols (eg. methanol, butanol), ketones (eg.cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water;carriers such as ground natural minerals (eg. kaolins, aluminas, talc,chalk) and ground synthetic minerals (eg. highly disperse silica,silicates); emulsifiers such as nonionic and anionic emulsifiers (eg.polyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates) and dispersants such as lignin-sulfite waste liquors andmethylcellulose.

Suitable surface-active substances are the alkali metal, alkaline earthmetal and ammonium salts of aromatic sulfonic acids, eg. lignosulfonic,phenolsulfonic, naphthalenesulfonic and dibutylnaphthalenesulfonic acid,and also of fatty acids, alkyl- and alkylarylsulfonates, alkyl-, laurylether and fatty alcohol sulfates, as well as salts of sulfated hexa-,hepta- and octadecanols, and also of fatty alcohol glycol-ether,condensation products of sulfonated naphthalene and its derivatives withformaldehyde, condensation products of naphthalene or of thenaphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyleneoctylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol,alkylphenol- or tributylphenylpolyglycol ethers, alkylaryl polyetheralcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkylethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignin-sulfite waste liquors or methylcellulose.

Powder, scattering and dusting compositions can be prepared by mixing orjoint grinding of the active substances with a solid carrier.

Granules, eg. coated, impregnated and homogeneous granules, can beprepared by binding the active compounds to solid carriers. Solidcarriers are mineral earths such as silica gel, silicic acids,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay,dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers, such asammonium sulfate, ammonium phosphate, ammonium nitrate, ureas andvegetable products, such as cereal flour, tree bark meal, wood meal andnutshell meal, cellulose powder or other solid carriers.

Examples of such preparations are:

I. a solution of 90 parts by weight of a compound I according to theinvention and 10 parts by weight of N-methyl-2-pyrrolidone, which issuitable for application in the form of very small drops;

II. a mixture of 10 parts by weight of a compound I according to theinvention, 70 parts by weight of xylene, 10 parts by weight of theaddition product of from 8 to 10 mol of ethylene oxide to 1 mol of oleicacid N-monoethanolamide, 5 parts by weight of calcium salt ofdodecylbenzene-sulfonic acid, 5 parts by weight of the addition productof 40 mol of ethylene oxide to 1 mol of castor oil; a dispersion isobtained by finely dispersing the solution in water.

III. an aqueous dispersion of 10 parts by weight of a compound Iaccording to the invention, 40 parts by weight of cyclohexanone, 30parts by weight of isobutanol, 20 parts by weight of the additionproduct of 40 mol of ethylene oxide to 1 mol of castor oil;

IV. an aqueous dispersion of 10 parts by weight of a compound Iaccording to the invention, 25 parts by weight of cyclohexanol, 55 partsby weight of a petroleum fraction of boiling point from 210° to 280° C.,and 10 parts by weight of the addition product of 40 mol of ethyleneoxide to 1 mol of castor oil;

V. a mixture, ground in a hammer mill, of 80 parts by weight, preferablyof a solid compound I according to the invention, 3 parts by weight ofthe sodium salt of diisobutylnaphthalene-2-sulfonic acid, 10 parts byweight of the sodium salt of a lignosulfonic acid from a sulfite wasteliquor and 7 parts by weight of powdered silica gel; a spray liquor isobtained by finely dispersing the mixture in water;

VI. an intimate mixture of 3 parts by weight of a compound I accordingto the invention and 97 parts by weight of finely divided kaolin; thisdusting composition contains 3% by weight of active compound;

VII. an intimate mixture of 30 parts by weight of a compound I accordingto the invention, 62 parts by weight of powdered silica gel and 8 partsby weight of liquid paraffin which has been sprayed onto the surface ofthis silica gel; this preparation gives the active compound goodadhesion;

VIII. a stable aqueous dispersion of 40 parts by weight of a compound Iaccording to the invention, 10 parts by weight of the sodium salt of aphenolsulfonic acid/urea/formaldehyde condensate, 2 parts by weight ofsilica gel and 48 parts by weight of water, which can be furtherdiluted;

IX. a stable oily dispersion of 20 parts by weight of a compound Iaccording to the invention, 2 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid, 8 parts by weight of fatty alcoholpolyglycol ether, 20 parts by weight of the sodium salt of aphenolsulfonic acid/urea/formaldehyde condensate and 50 parts by weightof a paraffinic mineral oil.

The novel compounds are distinguished by an outstanding activity againsta broad spectrum of phytopathogenic fungi, in particular from the classof Deuteromycetes, Ascomycetes, Phycomycetes and Basidiomycetes. Theyare systemically active in some cases and can be employed as foliar andsoil fungicides.

They are of particular importance for the control of a multiplicity offungi on various crop plants such as wheat, rye, barley, oats, rice,corn, grass, cotton, soybeans, coffee, sugar cane, grapes, fruit anddecorative plants and vegetable plants such as cucumbers, beans andcucurbits, and on the seeds of these plants.

The compounds are applied by treating the fungi or the seeds, plants,materials or the soil to be protected from fungal attack with afungicidally effective amount of the active compounds.

They are applied before or after the infection of the materials, plantsor seeds by the fungi.

The novel compounds are specifically suitable for the control of thefollowing plant diseases:

Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearumand Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha onapples, Uncinula necator on vines, Puccinia species on cereals,Rhizoctonia species on cotton and grass, Ustilago species on cereals andsugar cane, Venturia inaequalis (scab) on apples, Helminthosporiumspecies on cereals, Septoria nodorum on wheat, Botrytis cinerea (graymold) on strawberries, vines, decorative plants and vegetables,Cercospora arachidicola on groundnuts, Pseudocercosporellaherpotrichoides on wheat, barley, Pyricularia oryzae on rice,Phytophthora infestans on potatoes and tomatoes, Fusarium andVerticillium species on various plants, Plasmopara viticola on vines,Alternaria species on vegetables and fruit.

The novel compounds can also be employed in the protection of materials(preservation of wood), eg. against Paecilomyces variotii.

The fungicidal compositions in general contain from 0.1 to 95,preferably from 0.5 to 90, % by weight of active compound.

Depending on the type of effect desired, the application rates are from0.025 to 2, preferably from 0.1 to 1, kg of active compound per ha.

In seed treatment, amounts of active compound of from 0.001 to 50 g,preferably 0.01 to 10 g, per kilogram of seed are in general needed.

The compositions according to the invention can also be present asfungicides together with other active compounds in the application form,eg. with herbicides, insecticides, growth regulators, fungicides oralternatively with fertilizers.

On mixing with fungicides, in many cases an increase in the fungicidalspectrum of action is obtained here.

The following list of fungicides with which the compounds according tothe invention can be applied together is intended to illustrate thecombination possibilities, but not restrict them:

sulfur, dithiocarbamates and their derivatives, such as ferricdimethyldithiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate,manganese zinc ethylenediamine bisdithiocarbamate, tetramethylthiuramdisulfide, ammonia complex of zinc N,N-ethylenebisdithiocarbamate,ammonia complex of zinc N,N'-propylenebisdithiocarbamate, zincN,N'-propylenebisdithiocarbamate, N,N'-polypropylenebis(thiocarbamoyl)disulfide;

nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate,2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate,2-secbutyl-4,6-dinitrophenyl isopropyl carbonate, diisopropyl5-nitroisophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate,2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethylphthalimidophosphonothioate, 5-amino-1-bis(dimethylamino)-phosphinyl!-3-phenyl-1,2,4-triazole,2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo4,5-b!quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate,2-methoxycarbonylaminobenzimidazole, 2-(fur-2-yl)benzimidazole,2-(thiazol-4-yl)benzimidazole,N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,N-trichloromethylthiotetrahydrophthalimide,N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfamide,5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene,4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone,2-thiopyridine-1-oxide, 8-hydroxyquinoline or its copper salt,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide,2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide,2,4,5-trimethylfuran-3-carboxanilide,N-cyclohexyl-2,5-dimethylfuran-3-carboxamide,N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide,2-methylbenzanilide, 2-iodobenzanilide,N-formyl-N-morpholine-2,2,2-trichloroethyl acetal,piperazine-1,4-diylbis(1-(2,2,2-trichloroethyl))formamide,1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,

2,6-dimethyl-N-tridecylmorpholine or its salts,2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-3-(p-tert-butyl-phenyl)-2-methylpropyl!-cis-2,6-dimethylmorpholine, N-3-(p-tert-butylphenyl)-2-methylpropyl!-piperidine, 1-2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl!-1H-1,2,4-triazole,1-2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl!-1H-1,2,4-triazole,N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone,α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine,bis(p-chlorophenyl)-3-pyridinemethanol,1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene,1,2-bis(3-methoxycarbonyl-2-thioureido)benzene, α-2-(4-chlorophenyl)ethyl!-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol,1-3-(2-chlorophenyl)-1-(4-fluorophenyl)oxiran-2-yl-methyl!-1H-1,2,4-triazole,and

various fungicides, such as dodecylguanidine acetate, 3-3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl!glutarimide,hexachlorobenzene, DL-methyl-N-(2,6-dimethylphenyl)-N-2-furoylalaninate, DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alanine methylester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-amino-butyrolactone,DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester,5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin,N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,2-cyano- N-ethylaminocarbonyl-2-methoximino!acetamide, 1-2-(2,4-dichlorophenyl)pentyl!-1H-1,2,4-triazole,2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol,N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine,1-((bis(4-fluorophenyl)methyl-silyl)methyl)-1H-1,2,4-triazole,

strobilurins such as methyl E-methoximinoα-(o-tolyloxy)-o-tolyl!acetate, methyl E-2-{2-6-(2-cyanophenoxy)pyrimidin-4-yloxy!phenyl}-3-methoxyacrylate, methylE-methoximino α-(2,5-dimethoxy)-o-tolyl!acetamide,

anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl)aniline, N-4-methyl-6-(1-propynyl)pyrimidin-2-yl!aniline,N-(4-methyl-6-cyclopropylpyrimidin-2-yl)aniline,

phenylpyrroles such as4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile,

cinnamamides such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acrylicacid morpholide.

Synthesis Example

The procedure given in the synthesis example below can be used withmodification of the starting compound to obtain further representativesof the compounds I. The physical data of the correspondingly preparedproducts are given in Tables 4 and 5.

N-(Isopropoxycarbonyl)-L-valine(1-(β-naphthyl)ethyl)amide (compound No.4.2 in Table 4)

13.3 g (65 mmol) of diethyl cyanophosphate were added to a solution of14.2 g (65 mmol) of tert-butoxycarbonyl-L-valine and 13.6 g (65 mmol) of1-amino-1-(β-naphthyl)ethane in 300 ml of tetrahydrofuran. The mixturewas stirred at 0° C. for 1 hour and at 20° C. for 15 hours. The solventwas then removed and the residue was taken up using 300 ml of ethylacetate. The organic phase was washed with 200 ml in each case of 5%strength by weight sodium hydroxide solution, 10% strength hydrochloricacid, 10% strength by weight sodium hydrogen carbonate solution andwater, dried and concentrated. 18.0 g (49 mmol) ofN-(tert-butoxycarbonyl)-L-valine(1-(β-naphthyl)ethyl)amide (m.p. 97° C.)remained.

50 ml of trifluoroacetic acid were added with cooling to 17.0 g (46mmol) of this compound and the mixture was stirred at 0° C. for 1 hour.It was then warmed to 20° C., the trifluoroacetic acid was largelyremoved by distillation, the residue was taken up in 300 ml ofdichloromethane and this was washed with 200 ml each of 2N sodiumhydroxide solution, 5% strength by weight sodium hydrogen carbonatesolution and water. After drying and concentrating the organic phase,10.7 g (40 mmol) of L-valine (1-(β-naphthyl)ethyl)amide remained as ayellow viscous oil.

0.54 g (2.0 mmol) of this compound and 0.22 g (2.2 mmol) oftriethylamine in 40 ml of toluene were treated at 0° C. with 0.24 g (2.1mmol) of isopropyl chloroformate and the mixture was stirred at 20° C.for 15 hours. After removing the solvent, the residue was taken up using50 ml of ethyl acetate and the solution was washed with 40 ml in eachcase of 10% strength by weight hydrochloric acid, 10% strength by weightsodium hydrogen carbonate solution and water. After drying the organicphase, the solvent was removed. 0.58 g (1.6 mmol) of the title compoundremained as a colorless crystalline residue (m.p. 127° C.).

                  TABLE 4                                                         ______________________________________                                         ##STR9##                                                                                                            m.p. (°C.)                      No.  R.sup.1     X       n    R.sup.6  IR (cm.sup.-1)                         ______________________________________                                        4.1  C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                              0    H        97                                     4.2  CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                              0    H        127                                    4.3  CH(CH.sub.3)(C.sub.2 H.sub.5)                                                             CH.sub.3                                                                              0    H        134-142                                4.4  C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                              0    6-CH.sub.3                                                                             118-21                                 4.5  CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                              0    6-CH.sub.3                                                                             175-88                                 4.6  CH(CH.sub.3)C.sub.2 H.sub.5                                                               CH.sub.3                                                                              0    6-CH.sub.3                                                                             168-76                                 4.7  C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                              1    H        65-70                                  4.8  CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                              1    H        resin                                  4.9  CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                              0    6-OCH.sub.3                                                                            resin                                  4.10 C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                              0    1-CH.sub.3, 4-OMe                                                                      75-7                                   4.11 CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                              0    1-CH.sub.3, 4-OMe                                                                      127-8                                  ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                         ##STR10##                                                                                                           m.p. (°C.)                      No.    R.sub.1      X       n    R.sup.6                                                                             IR (cm.sup.-1)                         ______________________________________                                        5.1    C(CH.sub.3).sub.3                                                                          CH.sub.3                                                                              0    H     122-30                                 5.2    CH(CH.sub.3).sub.2                                                                         CH.sub.3                                                                              0    H     172-80                                 5.3    CH(CH.sub.3)C.sub.2 H.sub.5                                                                CH.sub.3                                                                              0    H     138-44                                 5.4    C(CH.sub.3).sub.3                                                                          CH.sub.3                                                                              0    4-Cl  72-9                                   5.5    CH(CH.sub.3).sub.2                                                                         CH.sub.3                                                                              0    4-Cl  196-8                                  5.6    CH(CH.sub.3)(C.sub.2 H.sub.5)                                                              CH.sub.3                                                                              0    4-Cl  166-9                                  ______________________________________                                    

Use examples

For the following tests, which are intended to show the fungicidalaction of the compounds I, an emulsion was used which consisted to 10%by weight of the active compound, and to 80% by weight of a mixture of:

70% by weight of cyclohexanol,

20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent havingemulsifying and dispersant action based on ethoxylated alkylphenols) and

10% by weight of Emulphor® EL (Emulan® EL, emulsifier based onethoxylated fatty alcohols).

The desired active compound concentration was set by diluting the thisemulsion with water.

Plasmopara viticola

Leaves of potted vines of the variety Muller-Thurgau were sprayed withaqueous spray liquor which contained 80% by weight of active compoundand 20% by weight of emulsifier in the dry substance. In order to assessthe duration of action of the active compounds, the plants were placedin a greenhouse for 8 days after the spray coating had dried on. Onlythen were the leaves infected with a zoospore suspension of Plasmoparaviticola (vine Peronospora). The vines were first placed for 48 hours ina chamber containing water vapor-saturated air at 24° C. and then for 5days in a greenhouse at from 20° to 30° C. After this time, the plantswere placed in the moist chamber again for 16 hours to accelerate escapefrom the sporangiophore. The extent of fungal outbreak on the bottoms ofthe leaves was then assessed visually.

In this test, the leaves of plants which had been treated with anaqueous preparation containing 250 ppm or 63 ppm of in each case one ofthe compounds Nos. 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 4.10,5.2, 5.4, 5.5 and 5.6 showed, in the case of 250 ppm of active compound,a fungal attack on 0 to 5% of the leaf surface and, at 63 ppm, on 0 to25% of the leaf surface. On the other hand, the leaves of the untreatedplants were attacked to 80%.

Phytophthora infestans

Leaves of potted plants of the variety Groβe Fleischtomate were sprayedwith aqueous spray liquor which contained 80% by weight of activecompound and 20% by weight of emulsifier in the dry matter. After 24hours, the leaves were infected with a zoospore suspension of the fungusPhytophthora infestans. The plants were then placed at from 16° to 18°C. in a chamber containing water vapor-saturated air. After 6 days, theattack on the untreated, but infected control plants had developed soseverely that it was possible to assess the fungicidal activity of thesubstances visually.

In this test, the leaves of plants which had been treated with anaqueous preparation containing 250 ppm or 63 ppm of in each case one ofthe compounds Nos 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.2, 5,4and 5.6 showed a fungal attack on 0 to 15% of the leaf surface. On theother hand, the leaves of the untreated plants were attacked to 90%.

We claim:
 1. A carbamoylcarboxamide of the general formula I ##STR11##and its salts, where the variables have the following meanings: R¹ is C₁-C₈ -alkyl, C₂ -C₈ -alkenyl or C₂ -C₈ -alkynyl, it being possible forthese radicals to be partially or completely halogenated and/or to carryone to three of the following groups: cyano, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkoxycarbonyl, C₃ -C₇-cycloalkyl, C₃ -C₇ -cycloalkenyl, aryl, aryloxy and heteroaryl, itbeing possible for the cyclic and aromatic rings of these groups tocarry one to three of the following substituents: halogen, cyano, C₁ -C₄-alkyl, C₁ -C₄ -alkoxyalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkoxycarbonyl, aryl, aryloxyand heteroaryl,C₃ -C₇ -cycloalkyl or C₃ -C₇ -cycloalkenyl, it beingpossible for these radicals to be partially or completely halogenatedand/or to carry one to three of the following groups: cyano, C₁ -C₄-alkyl, C₁ -C₄ -alkoxyalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkoxycarbonyl, aryl, aryloxyand aryl-(C₁ -C₄)-alkyl, it being possible for the aromatic rings ofthese groups in turn to carry one to three of the followingsubstituents: halogen, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-alkyl, C₁-C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio,C₁ -C₄ -alkoxycarbonyl, aryl and aryloxy, a nonaromatic 4- to 8-memberedring which, as ring members, in addition to carbon can further containone or two of the heteroatoms oxygen, sulfur and nitrogen, it beingpossible for the carbon atoms in the ring to carry one or two of thefollowing groups: halogen, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxyalkyl, C₁-C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio,C₁ -C₄ -alkoxy-carbonyl, aryl and aryloxy, and the second and anyfurther nitrogen atom as a heteroatom in the ring carrying hydrogen or aC₁ -C₄ -alkyl group; R² is hydrogen, or C₁ -C₈ -alkyl, or C₃ -C₇-cycloalkyl which can be partially or completely halogenated; R³ is C₁-C₈ -alkyl, it being possible for this radical to carry one to three ofthe following groups: halogen, cyano, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio and C₁ -C₄ -alkoxycarbon C₃ -C₇-cycloalkyl or phenyl-(C₁ -C₄)-alkyl, it being possible for the rings ofthese radicals to carry one to three of the following groups: halogen,cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxyalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkoxycarbonyl,aryl and aryloxy; R⁴ is hydrogen or one of the radicals R³ or R³ and R⁴,together with the C atom to which they are bonded, are a 4- to8-membered ring which, as ring members, in addition to carbon canfurther contain one or two of the heteroatoms oxygen, sulfur andnitrogen, it being possible for the carbon atoms in the ring to carryone or two of the following groups: halogen, cyano, C₁ -C₄ -alkyl, C₁-C₄ -alkoxyalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy,C₁ -C₄ -alkylthio, C₁ -C₄ -alkoxycarbonyl, aryl and aryloxy, andnitrogen as a heteroatom carrying hydrogen or a C₁ -C₄ -alkyl group; R⁵independently of these is one of the radicals R² ; X independently ofone another is hydrogen, C₁ -C₈ -alkyl and/or C₂ -C₈ -alkenyl, it beingpossible for these radicals to be partially or completely halogenatedand/or to carry one to three of the following groups: cyano, C₁ -C₄-alkoxyalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁-C₄ -alkylthio and C₁ -C₄ -alkoxycarbonyl, aryl and aryloxy; Yindependently of one another and of these is one of the radicals X; p,qindependently of one another are 0, 1 or 2, except that neither may bothbe 0; R⁶ is halogen, cyano, nitro, C₁ -C₈ -alkyl, C₁ -C₄ -alkoxyalkyl,C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄-alkylthio, C₁ -C₄ -haloalkylthio or a phenyl group bonded via oxygen orsulfur, which is unsubstituted or can carry one to three of thefollowing substituents: halogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy, whereR⁶ for r>1 can be various radicals from those mentioned; r is 0, 1, 2 or3.
 2. A process for preparing compounds of the general formula I asclaimed in claim 1, which comprises reacting a carbamoylcarboxylic acidof the general formula II ##STR12## with an amine of the general formulaIII ##STR13##
 3. A process for preparing compounds of the generalformula I as claimed in claim 1, which comprisesa) converting acarbamoylcarboxamide of the general formula I ##STR14## where the groupR¹ --O--(CO) is a protective group which can be removed in a mannerknown per se, to an amino acid amide IV ##STR15## and b) reacting theamino acid amide IV thus obtained with a chloroformic acid ester of thegeneral formula V ##STR16## in the presence of a base.
 4. A compositionsuitable for controlling harmful fungi, containing at least one liquidor solid carrier and a fungicidally effective amount of at least onecompound of the general formula I or a salt of I as claimed in claim 1.5. A process for preparing compositions suitable for controlling harmfulfungi, which comprises mixing a fungicidally effective amount of atleast one compound of the general formula I or a salt of I as claimed inclaim 1 and at least one inert liquid or solid carrier and, if desired,at least one adjuvant.
 6. A method of controlling harmful fungi, whichcomprises treating the harmful fungi, their habitat or the plants,surfaces, materials or spaces to be kept free from them with afungicidally effective amount of at least one compound of the generalformula I or one of its salts as claimed in claim
 1. 7. A method ofcontrolling harmful fungi, which comprises treating the harmful fungi,their habitat or the plants, surfaces, material or spaces to be keptfree from them with a fungicidally effective amount of at least onecomposition as claimed in claim 4.